When you use the mass upload roster feature, you are only able to add one position. There should be an option to add another position by adding a special character between the two positions, like the "|" just like what we do with mass schedule template for the identifications of which team pages the game would go.
|Which sport(s) does this apply to:||Not Sport Specific|
You can do this today. The separator is a comma, not a pipe. Here is an example screenshot of what the upload file looks like.